Selectivity of photolytic reaction of 4-azidobenzoic acid with N-methylbutyramide in aqueous medium; a model of photochemical modification of proteins with arylazides

N. A. Kravchenko, L. G. Menchikov, I. A. Cherkasov

N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

Abstract: Photolytic reaction of 4-azidobenzoic acid (ABA) with N-methylbutyramide(MBA) in aqueous solution is investigated and shown to yield 2-(N-methylbutyramido)-3H-azepine-5-carboxylic acid along with 3H -azepin-2-one-5-carboxylic acid as a product of the reaction with water. The observed conversion of MBA is considered as a model of a nonspecific photochemical modification of proteins (e. g., human IgG) with ABA, apparently via attack on N-H bonds of the peptide chain.

Russian Journal of Bioorganic Chemistry 1991, 17 (2):283-284

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